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WO2006107802A1 - Agents de scellement barrieres cycloaliphatiques durcissables par rayonnement - Google Patents

Agents de scellement barrieres cycloaliphatiques durcissables par rayonnement Download PDF

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Publication number
WO2006107802A1
WO2006107802A1 PCT/US2006/012181 US2006012181W WO2006107802A1 WO 2006107802 A1 WO2006107802 A1 WO 2006107802A1 US 2006012181 W US2006012181 W US 2006012181W WO 2006107802 A1 WO2006107802 A1 WO 2006107802A1
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Prior art keywords
curable
barrier sealant
resin
sealant according
curable barrier
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English (en)
Inventor
Donald E. Herr
Shengqian Kong
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National Starch and Chemical Investment Holding Corp
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National Starch and Chemical Investment Holding Corp
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Priority to EP06749107A priority Critical patent/EP1866960B1/fr
Priority to AT06749107T priority patent/ATE455371T1/de
Priority to JP2008505403A priority patent/JP5575393B2/ja
Priority to KR1020077024674A priority patent/KR101332702B1/ko
Priority to CN2006800108791A priority patent/CN101151726B/zh
Priority to DE602006011724T priority patent/DE602006011724D1/de
Publication of WO2006107802A1 publication Critical patent/WO2006107802A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/12—Polythioether-ethers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/02—Containers; Seals
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/02—Containers; Seals
    • H01L23/10—Containers; Seals characterised by the material or arrangement of seals between parts, e.g. between cap and base of the container or between leads and walls of the container
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/842—Containers
    • H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants

Definitions

  • This invention relates to barrier adhesives, sealants, encapsulants, and coatings for use in electronic and opto-electronic devices.
  • adhesives, sealants, encapsulants and coatings are similar materials, all having adhesive, sealant, encapsulants and coating properties and functions. When any one is recited, the others are deemed to be included.
  • Radiation curable materials have found increased use as coatings, adhesives, and sealants over the past three decades for reasons including low energy consumption during cure, rapid cure speed through both radical and cationic mechanisms, low curing temperature, wide availability of curable materials, and the availability of solvent-free products. These benefits have made such products especially suited for rapidly adhering and sealing electronic and optoelectronic devices that are temperature sensitive or cannot conveniently withstand prolonged curing times. Optoelectronic devices particularly are often thermally sensitive and may need to be optically aligned and spatially immobilized through curing in a very short time period.
  • Figure 1 which discloses the use of a radiation curable perimeter sealant (1) to bond a metal or glass lid (2) over an organic light emitting diode (OLED) stack (3) fabricated on a glass substrate (4).
  • OLED organic light emitting diode
  • a typical device also contains an anode (5), a cathode (6), and some form of electrical interconnect between the OLED pixel/device and external circuitry (7).
  • no particular device geometry is specified or required aside from one which incorporates an adhesive/sealant material such as a perimeter sealant (1).
  • both the glass substrate and the metal/glass lid are essentially impermeable to oxygen and moisture, and the sealant is the only material that surrounds the device with any appreciable permeability.
  • moisture permeability is very often more critical than oxygen permeability; consequently, the oxygen barrier requirements are much less stringent, and it is the moisture barrier properties of the perimeter sealant that are critical to successful performance of the device.
  • P water vapor transmission rate
  • WVTR water vapor transmission rate
  • permeability coefficient e.g. g.mil/(100 in 2 .day.atm)
  • permeation coefficient e.g. g.mil/(100 in z .day) at a given temperature and relative humidity
  • D diffusion term
  • S solubility term
  • the solubility term reflects the affinity of the barrier for the permeant, and, in relation to water vapor, a low S term is obtained from hydrophobic materials.
  • the diffusion term is a measure of the mobility of a permeant in the barrier matrix and is directly related to material properties of the barrier, such as free volume and molecular mobility. Often, a low D term is obtained from highly crosslinked or crystalline materials (in contrast to less crosslinked or amorphous analogs). Permeability will increase drastically as molecular motion increases (for example as temperature is increased, and particularly when the T 9 of a polymer is exceeded).
  • Logical chemical approaches to producing improved barriers must consider these two fundamental factors (D and S) affecting the permeability of water vapor and oxygen.
  • Figure 1 is a depiction of a Perimeter Sealed Optoelectronic Device
  • Figure 2 is a depiction of a Cycloaliphatic Vinyl Ether Synthesis
  • Figure 3 is PhotoDSC Analysis of the Basic Q43/TAIC Thiol-ene System (Formulation 7); and
  • Figure 4 is Real-Time UV-FT-IR Analysis of the Basic Q43/TAIC Thiol-ene System (Formulation 7).
  • the inventors have discovered that certain resin and resin/filler systems provide superior barrier performance through the incorporation of a radiation-curable material that possesses a cycloaliphatic backbone.
  • cycloaliphatic barrier materials may be used alone or in combination with other resins and various fillers.
  • the resulting compositions exhibit a commercially useful cure rate, a balance of high crosslink density, rigidity, and molecular packing (low permeant mobility/diffusivity term, D), hydrophobicity (low water solubility term, S), and adhesion (strong adhesive/substrate interfaces) to make them effective for use in sealing and encapsulating electronic, optoelectronic, and MEMS devices.
  • This invention is a curable barrier adhesive or sealant comprising: (a) a curable resin characterized in that it has (i) a cycloaliphatic (or alicyclic) backbone, and (ii) at least one reactive functional group present at a level that provides an equivalent weight of less than 400 grams per mole of reactive functional group, and (b) an initiator.
  • a curable resin characterized in that it has (i) a cycloaliphatic (or alicyclic) backbone, and (ii) at least one reactive functional group present at a level that provides an equivalent weight of less than 400 grams per mole of reactive functional group, and (b) an initiator.
  • at least one reactive functional group is deemed to mean one or more of the same type of reactive functional group and/or one or more types of reactive functional groups; the overall functional group equivalent weight will remain less than 400 grams per mole.
  • the radiation-curable barrier adhesive or sealant further comprises (c) a reactive or non-reactive resin (other than the resin with a cycloaliphatic backbone).
  • the curable barrier adhesive or sealant further comprises (d) a filler.
  • Radiation curable sealants are often preferred (for the reasons noted in the Background section) but thermally curable sealants are also useful depending on the specific application.
  • the term radiation is used to describe actinic electromagnetic radiation. Actinic radiation is defined as electromagnetic radiation that induces a chemical change in a material, and for purposes within this specification will also include electron-beam curing. In most cases electromagnetic radiation with wavelengths in the ultraviolet (UV) and/or visible regions of the spectrum are most useful.
  • cycloaliphatic or alicyclic refer generally to a class of organic compounds containing carbon and hydrogen atoms joined to form one or more rings, which may contain other atoms, such as, halogens (e.g. Cl, Br, I), heteroatoms (e.g. O, S, N), or substituent groups (e.g. OR, SR, NR 2 in which R is a linear or branched alkyl or cycloalkyl or aryl group).
  • cycloaliphatic resins are defined as resins that contain a cyclic carbon-based ring structure in their backbone, which cyclic carbon backbone may have heteroatoms within the backbone or attached to it.
  • the cycloaliphatic resin backbone be composed primarily of carbon, hydrogen and halogen atoms.
  • the cycloaliphatic radiation-curable resins (a) may be small molecules, oligomers, or polymers depending on the desired end use application and materials properties.
  • Suitable resins containing a cycloaliphatic backbone are any that after crosslinking permit close packing of relatively rigid molecular segments between the crosslinked portions of the matrix. (The molecular segments are those derived from the uncured cycloaliphatic backbone.)
  • the cycloaliphatic molecule will have a generic structure depicted as:
  • L is a linking group independently selected from the group consisting of
  • R is a linear or branched alkyl, cycloalkyi, aryl, heteroaryl, silane or siloxane and may contain heteroatoms (such as O 1 S, and N);
  • X is a reactive group independently selected from epoxies, selected from glycidyl epoxy, aliphatic epoxy, and cycloaliphatic epoxy; acrylate and methacrylate; itaconate; maleimide; vinyl, propenyl, crotyl, allyl, and propargyl ether and thio-ethers of those groups; maleate, fumarate, and cinnamate esters; styrenic; acrylamide and methacrylamide; chalcone; thiol; allyl, alkenyl, and cycloalkenyl; n, k, and I equal 0 or 1 ; and y equals 1 to 10.
  • the reactive group X on the radiation-curable resin is vinyl ether, acrylate or
  • Particularly suitable compounds with cycloaliphatic backbones are selected from the group consisting of
  • X can be attached to the cycloaliphatic backbone by a direct bond or can be a part of the cycloaliphatic backbone.
  • Other suitable compounds include those selected from the group having the structures:
  • R is hydrogen, an alkyl group, a heteroalkyl group, or a halogen.
  • suitable resins include dicyclopentadiene (DCPD) dimethylol diacrylate and the cycloaliphatic vinyl ether derived from DCPD dimethylol as shown in Figure 2.
  • Additional suitable radiation-curable resins with cycloaliphatic backbones are those selected from the group consisting of
  • the curable resin for the moisture-barrier sealant is the curable resin for the moisture-barrier sealant
  • R is hydrogen, alkyl (e.g. methyl) or halogen (e.g. chlorine).
  • halogen e.g. chlorine
  • moisture-barrier sealant is in which R is hydrogen, alkyl (e.g. methyl) or halogen (e.g. chlorine).
  • suitable curable functionalities on the resins (a) include any known to those with experience in the field of UV and thermally curable materials and filled polymer composites.
  • Common curable functionalities include, but are not limited to, epoxies, selected from glycidyl epoxy, aliphatic epoxy, and cycloaliphatic epoxy; acrylate and methacrylate; itaconate; maleimide; vinyl, propenyl, crotyl, allyl, and propargyl ether and thio-ethers of those groups; maleate, fumarate, and cinnamate esters; styrenic; acrylamide and methacrylamide; chalcone; thiol; allyl, alkenyl, and cycloalkenyl.
  • the polymerization mechanism upon irradiation or heating is not limited, but is typically either a radical or cationic process.
  • the inventors have found, within predefined boundaries of overall crosslink density, that the type of reactive functional groups present are not as critical to barrier properties as the nature of the backbone to which those reactive functional groups are attached.
  • the reactive functionality will be present at a level that provides an equivalent weight of less than 400 grams per mole of reactive functional group.
  • the definition of equivalent weight is that commonly used by those skilled in the art: it is the molecular weight divided by the total functionality (e.g. epoxy, acrylate, maleimide, etc.). Equivalent weight is the mass per mole of reactive group.
  • the permeant has low solubility in the barrier material.
  • the barrier material is hydrophobic, this results in low moisture solubility in the cured adhesive/sealant barrier material, which reduces moisture permeability.
  • hydrophobic materials are not necessarily good barrier materials, particularly if they have low crosslink density (high uncured equivalent weight) or exhibit high mobility/high free volume in the cured state.
  • the term hydrophobic means absorbing less than 5.00 weight % water at 85°C and 85% relative humidity (RH).
  • the cycloaliphatic-based compositions tend to be hydrophobic as they are primarily hydrocarbon in nature. This hydrophobicity results in low moisture solubility in the cured material, which also reduces moisture permeability.
  • the use of primarily cycloaliphatic materials to achieve this combination of low permeant mobility and low moisture solubility is novel and unexpected among curable barrier materials.
  • Both suitable radiation curable resins and suitable photoinitiators for radiation curable resins may be any of those commonly described in the open literature. Representative examples may be found in literature sources such as Fouassier, J-P., Photoinitiation, Photopolymerization and Photocuring Fundamentals and Applications 1995, Hanser/Gardner Publications, Inc., New York, NY. Chapter 6 is a particularly useful overview of the various classes of radiation curable resins and photoinitiators used by those practiced in the art. Exemplary photoinitiators are disclosed in Ionic Polymerizations and Related processes, 45-60, 1999, Kluwer Academic Publishers; Netherlands; J.E. Puskas et al. (eds.). Curing mechanisms may be any of those described therein and most frequently the resin system cures through either a radical or cationic mechanism.
  • the initiator (b) will be a photoinitiator.
  • photoinitiator (b) for the inventive radiation curable barrier adhesives is familiar to those skilled in the art of radiation curing.
  • the selection of an appropriate photoinitiator system is highly dependent on the specific application in which the barrier sealant is to be used.
  • a suitable photoinitiator is one that exhibits a light absorption spectrum that is distinct from that of the resins, fillers, and other additives in the radiation curable system.
  • the sealant must be cured through a cover or substrate, the photoinitiator will be one capable of absorbing radiation at wavelengths for which the cover or substrate is transparent.
  • the photoinitiator must have significant absorbance above ca. 320 nm, which is the UV cut-off of sodalime glass. In some cases, it is anticipated that the use of photosensitizers will be helpful.
  • either Type 1 for systems that cure via a radical mechanism
  • I (cleavage) or Type Il (H abstraction) radical photoinitiators may be used.
  • Small molecule, polymeric, or polymerizeable photoinitiators may be used.
  • common cleavage photoinitiators such as those offered by Ciba Specialty Chemicals, are useful.
  • Preferred photoinitiators include lrgacure 651 , lrgacure 907, and lrgacure 819, all sold by Ciba.
  • a preferred class of photoinitiators are polymer-bound aromatic ketones, or polymeric Type Il photoinitiators.
  • Such systems do not produce small molecule photo by-products, and therefore tend to produce less odor, outgassing, and extractable components upon UV cure.
  • Such systems may or may not require a photosensitizer, depending on the specific application and resin system used.
  • Preferred cationic photoinitiators include diaryliodonium salts and triarylsulfonium salts.
  • Well known commercially available examples include UV9380C (GE Silicones), PC2506 (Polyset), Rhodorsil 2074 (Rhodia), and UVI-6974 (Dow). If curing through certain covers or substrates, an appropriate photosensitizer should be used to assure adequate light absorption by the photoinitiating system.
  • Preferred sensitizers for diaryliodonium salts are isopropylthioxanthone (often sold as a mixture of 2- and 4-isomers) and 2-chloro-4-propoxythioxanthone.
  • cationic photoinitiating system for a particular curing geometry and resin system is known to those skilled in the art of cationic UV curing, and is not limited within the scope of this invention.
  • Less common initiating systems such as photogenerated bases (e.g. photogenerated amines or photogenerated polythiols) are also anticipated in cases where such basic catalysts, initiators, and curing agents are appropriate.
  • the inventive cycloaliphatic barrier adhesives may be cured thermally as well as photochemically. Appropriate thermal initiators are well known to those skilled in the art of thermoset chemistry, and will vary widely depending on resin type, curing mechanism, and end use of the barrier sealant.
  • azo-type initiators such as 2,2'- azobisisobutyronitrile (sold by various vendors, including DuPont as Vazo 64), peroxyketals such as 1 , 1 '-di(£-amylperoxy)cyclohexane (sold by Witco as USP- 90MD), peresters such as f-amyl peroxypivalate (sold by Akzo as Trigonox 125-C75), and alkylperoxides, such as, di-cumyl peroxide (sold by various vendors such as Witco).
  • azo-type initiators such as 2,2'- azobisisobutyronitrile (sold by various vendors, including DuPont as Vazo 64), peroxyketals such as 1 , 1 '-di(£-amylperoxy)cyclohexane (sold by Witco as USP- 90MD), peresters such as f-amyl peroxypivalate (sold by Akzo
  • thermal cationic initiators are also contemplated.
  • such catalysts include any sort of Br ⁇ nsted or Lewis acids, often in the form of a latent thermal acid generator.
  • latent thermal acid generators include, but are not limited to, diaryliodonium salts, benzylsulfonium salts, phenacylsulfonium salts, N-benzylpyridinium salts, N-benzylpyrazinium salts, N-benzylammonium salts, phosphonium salts, hydrazinium salts, and ammonium borate salts.
  • An example of a useful diaryliodonium salt thermal cationic initiator is PC2506 (Polyset).
  • Diaryliodonium salts can often be accelerated (made to initiate at low temperature with acceptable latency) by adding electron donating co-initiators such as benzopinacol. The initiation mechanism then essentially becomes one of redox reduction of the diaryliodonium salt by a species generated through the thermal decomposition of the co-initiator.
  • co-initiators such as benzopinacol.
  • Other representative examples of thermally activated cationic catalysts include sulfonates and sulfonate salts (available from King Industries under the tradename of Nacure and K-cure).
  • the cycloaliphatic resin component may optionally be blended with one or more other reactive or non-reactive resin components (c). These optional resins may be used to modify specific properties of the compositions, such as toughness, flexibility, adhesion to certain substrates, or to minimize weight loss during or after cure. Typically, it is beneficial to use as much cycloaliphatic material as is practical.
  • the amount of these other resin components will varying depending on the application, processing conditions, and barrier requirements, but will generally fall within the range of 1-90% of the total resinous portion of the barrier sealant composition.
  • the second (non-cycloaliphatic) resin component may contain any of the reactive groups described previously for the cycloaliphatic resin component.
  • common reactive optional resins include, but are not limited to epoxy resins, acrylic resins, maleimide resins, vinyl and propargyl ether resins, fumarate esters, maleate esters, cinnamate esters, chalcones, polythiols, and allylated molecules.
  • Representive epoxy resins are glycidyl ethers and cycloaliphatic epoxies.
  • Various sources and variations of glycidyl ethers are well known to those skilled in the art.
  • Representative aromatic liquid glycidyl ethers include epoxy resins such as Epikote 862 (essentially bisphenol F diglycidyl ether) or Epikote 828 (essentially bisphenol A diglycidyl ether).
  • Preferred solid glycidyl ethers include Epon 1031 , Epon 164, SU-8, DER 542 (brominated bisphenol A diglycidyl ether), RSS 1407 (tetramethylbiphenyldiglycidyl ether), and Erisys RDGE (resorcinol diglycidyl ether). All of these Epikote ® and Epon ® glycidyl ethers are available from Resolution Performance Products. Erisys RDGE ® is available from CVC Specialty Chemicals, Inc.
  • Representative non-aromatic glycidyl epoxy resins include EXA-7015 available from Dainippon Ink & Chemicals (hydrogeneated bisphenol A diglycidylether).
  • Representative cycloaliphatic epoxy resins include ERL 4221 and ERL 6128 available from Dow Chemical Co.
  • Optional fillers (d) may vary widely and are well known to those skilled in the art of composite materials. Common fillers include, but are not limited to ground quartz, fused silica, amorphous silica, talc, glass beads, graphite, carbon black, alumina, clays, mica, vermiculite, aluminum nitride, and boron nitride. Metal powders and flakes consisting of silver, copper, gold, tin, tin/lead alloys, and other alloys are contemplated. Organic filler powders such as poly(tetrachloroethylene), poly(chlorotriflouroethylene), and poly(vinylidene chloride) may also be used.
  • Fillers that act as desiccants or oxygen scavengers including but not limited to, CaO, BaO 1 Na 2 SO 4 , CaSO 4 , MgSO 4 , zeolites, silica gel, P 2 O 5 , CaCI 2 , and AI 2 O 3 may also be utilized.
  • EXAMPLE 1 UV CURABLE CYCLOALIPHATIC ACRYLIC BARRIERS.
  • Several UV curable acrylate compositions were formulated by mixing several structurally distinct acrylate resins with a polythiol, a photoinitiator, and fumed silica in parts by weight as shown in Table 1. [0044]
  • HDDA is hexanediol diacrylate
  • TMPTA is trimethylolpropane triacrylate
  • pBD DMA is poly(butadiene)dimethacrylate
  • DCPDDA is dicyclopentadienedimethylol diacrylate.
  • Q-43 is pentaerythritol tris(3-mercapto-propionate) and is a polythiol, which acts to reduce oxygen inhibition and as a flexibilizer.
  • the Q-43 polythiol has the structure:
  • the photoinitiator used was lrgacure 651 , obtained from Ciba
  • the fumed silica acts as a thixotrope to allow high quality films to be formed and purged with nitrogen prior to cure without dewetting the release liner substrate.
  • the three resin systems 1 through 3 have low equivalent weight, and are thus expected to produce highly crosslinked materials upon cure. Yet, the cycloaliphatic resin-based system (formulation 3), exhibits significantly lower bulk permeability than the other two acrylate formulations (formulations 1 and 2). Also, HDDA (formulaton 1) and DCPDDA (formulation 3) are both considered hydrophobic acrylate materials (TMPTA, formulation 2, is fairly hydrophobic as well), yet again the cycloaliphatic resin provides superior moisture barrier properties.
  • the HDDA, TMPTA, and pBD DMA molecules exhibit some properties that lead one to expect that they might produce good moisture barriers, it is not just hydrophobicity or just high crosslink density, but the unique combination of backbone structure/packing and high crosslink density that provide the DCPDDA-based formulation 3 with clearly superior moisture barrier properties.
  • UV curable thiol-ene formulations were prepared according to Table 3 using the same polythiol (Q-43) as in Example 1 , various ene components, and a photoinitiator.
  • Q-43 is pentaerythritol tetrakis(3-mercpatopropionate); DAC is diallylchlorendate; TAIC is triallyl isocyanurate (with 100 ppm BHT stabilizer); TABPA is tetraallyl bisphenol A.
  • the photoinitiator was lrgacure 651, obtained from Ciba Specialty
  • the internal double bond of DAC is not as reactive as its allyl groups, and as such the trifunctional ene TAIC should produce higher crosslink densities relative to DAC as indicated by photoDSC exotherm.
  • the data show that the TAIC-containing formulations exhibit inferior moisture barrier properties relative to the DAC-containing formulations, even though the TAIC-containing formulations have higher crosslink densities when cured relative to the DAC films.
  • the cycloaliphatic nature of the DAC ene is presumed to play a role in this phenomenon, and the chlorination of DAC may contribute favorably to its moisture barrier properties as well.
  • CAVE, CHVE, and BDDVE should have similar hydrophobicity, as should their respective cured formulations.
  • all three of these formulations exhibit both high crosslink density (low vinyl ether equivalent weight) and hydrophobicity
  • the CAVE and CHVE- based formulations which are also cycloaliphatic, exhibit better moisture barrier performance.
  • hydrophobicity it is the unique combination of high crosslink density and cycloaliphatic backbone properties that produces superior barrier performance.
  • a syringe dispensable, UV-curable barrier sealant was formulated under short wavelength-visible filtered lighting using the components as shown in Table 7.
  • the resin components were combined and mixed to dissolve the ITX photosensitizer.
  • the silica fillers were subsequently added and hand mixed until bulk wet-out was obtained.
  • the paste was then milled at least two times on a three-roll mill using a gap setting less than 0.5 mil between each roll. The paste was considered adequately milled when no particles larger than 10 ⁇ m were observed in a Hegeman gauge test. This product was allowed to age in the dark for at least 24 hours prior to checking rheology or testing for material properties.
  • This adhesive composition can be used to seal various types of optoelectronic devices in which substrates such as glass, metal, or polymeric films are bonded.
  • sodalime glass die were bonded to sodalime glass substrates to simulate a perimeter sealed "glass-to-glass" OLED device.
  • Adhesive was dispensed onto a PTFE-coated Al substrate, and a ca. 4 mil film was formed using a drawdown bar. Glass die were placed on this wet film, removed, and subsequently placed on a cleaned glass substrate with light pressure to simulate a "pick and place” type robotic packaging process.
  • Samples were then inverted and irradiated with UV light through the glass substrate to produce a cured glass-to-glass bond. UV curing was performed in a Dymax stationary curing unit. The UV dose was 3J UVA/cm 2 , at an intensity of ca.
  • CAVE cycloaliphatic vinyl ether
  • CAVE contributes hydrophobicity (as evidenced by low saturation moisture uptake/weight gain at 85°C/85% RH), good crosslink density due to its low equivalent weight and multifunctionality (as evidenced by its relatively high T 9 for a UV cured formulation and the excellent shear adhesion strength of the formulation), excellent UV reactivity (evidenced by low TGA weight loss of cured films), and a bulk moisture permeation coefficient lower than currently available perimeter sealant products known to the inventors.
  • the improved moisture barrier properties arise from the material's high crosslink density and rigid backbone (low permeant mobility) combined with the overall hydrophobicity of the composite (low permeant solubility).
  • This adhesive composition can be used to seal various types of optoelectronic devices that bond substrates such as glass, metal, or polymeric films. As an example, sodalime glass die were bonded to sodalime glass substrates to simulate a perimeter sealed "glass-to-glass" OLED device.
  • Adhesive was dispensed onto a PTFE-coated Al substrate, and a ca. 4 mil film was formed using a drawdown bar. Glass die were placed on this wet film, removed, and subsequently placed on a glass substrate with light pressure to simulate a "pick and place” type packaging process.
  • BMM has the following structure:
  • BMI-4 has the following structure:
  • EXAMPLE 7 AROMATIC EPOXY/CYCLOALIPHATIC EPOXY-BASED UV-
  • a syringe dispensable, UV-curable barrier sealant was formulated under short wavelength-visible filtered lighting using the components as shown in
  • This adhesive composition can be used to seal various types of optoelectronic devices in which substrates such as glass, metal, or polymeric films are bonded.
  • sodalime glass die were bonded to sodalime glass substrates to simulate a perimeter sealed "glass-to-glass” OLED device.
  • Adhesive was dispensed onto a PTFE-coated Al substrate, and a ca. 4 mil film was formed using a drawdown bar. Glass die were placed on this wet film, removed, and subsequently placed on a cleaned glass substrate with light pressure to simulate a "pick and place" type robotic packaging process.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • General Physics & Mathematics (AREA)
  • Power Engineering (AREA)
  • Computer Hardware Design (AREA)
  • Engineering & Computer Science (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Physics & Mathematics (AREA)
  • Sealing Material Composition (AREA)
  • Electroluminescent Light Sources (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention concerne un agent de scellement barrière durcissable comprenant une résine durcissable contenant un squelette cycloaliphatique et un groupe fonctionnel réactif présent à un taux fournissant un poids équivalent inférieur à 400 grammes par mole de groupe fonctionnel réactif.
PCT/US2006/012181 2005-04-04 2006-04-03 Agents de scellement barrieres cycloaliphatiques durcissables par rayonnement Ceased WO2006107802A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP06749107A EP1866960B1 (fr) 2005-04-04 2006-04-03 Agents de scellement barrieres cycloaliphatiques durcissables par rayonnement
AT06749107T ATE455371T1 (de) 2005-04-04 2006-04-03 Strahlungshärtbare cycloaliphatische sperrdichtstoffe
JP2008505403A JP5575393B2 (ja) 2005-04-04 2006-04-03 放射線硬化性環式脂肪族バリアシーラント
KR1020077024674A KR101332702B1 (ko) 2005-04-04 2006-04-03 방사선 경화성 지환족 장벽 밀봉재
CN2006800108791A CN101151726B (zh) 2005-04-04 2006-04-03 可辐射固化脂环族防渗密封胶
DE602006011724T DE602006011724D1 (de) 2005-04-04 2006-04-03 Strahlungshärtbare cycloaliphatische sperrdichtstoffe

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/098,115 US20060223937A1 (en) 2005-04-04 2005-04-04 Radiation curable cycloaliphatic barrier sealants
US11/098,115 2005-04-04

Publications (1)

Publication Number Publication Date
WO2006107802A1 true WO2006107802A1 (fr) 2006-10-12

Family

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PCT/US2006/012181 Ceased WO2006107802A1 (fr) 2005-04-04 2006-04-03 Agents de scellement barrieres cycloaliphatiques durcissables par rayonnement

Country Status (9)

Country Link
US (2) US20060223937A1 (fr)
EP (1) EP1866960B1 (fr)
JP (1) JP5575393B2 (fr)
KR (1) KR101332702B1 (fr)
CN (1) CN101151726B (fr)
AT (1) ATE455371T1 (fr)
DE (1) DE602006011724D1 (fr)
TW (1) TWI406364B (fr)
WO (1) WO2006107802A1 (fr)

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WO2020101319A1 (fr) * 2018-11-12 2020-05-22 주식회사 엘지화학 Composition de produit d'étanchéité
US11291222B2 (en) 2013-03-15 2022-04-05 Cargill, Incorporated Carbohydrate compositions
WO2022146099A1 (fr) * 2020-12-31 2022-07-07 주식회사 엘지화학 Composition d'agent d'étanchéité et dispositif optoélectronique organique la comprenant

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WO2007111607A1 (fr) * 2006-03-29 2007-10-04 National Starch And Chemical Investment Materiau d'etancheite/adhesif a base de caoutchouc durcissable par rayonnements
US11291222B2 (en) 2013-03-15 2022-04-05 Cargill, Incorporated Carbohydrate compositions
WO2020101319A1 (fr) * 2018-11-12 2020-05-22 주식회사 엘지화학 Composition de produit d'étanchéité
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Also Published As

Publication number Publication date
CN101151726A (zh) 2008-03-26
DE602006011724D1 (de) 2010-03-04
EP1866960B1 (fr) 2010-01-13
TWI406364B (zh) 2013-08-21
JP5575393B2 (ja) 2014-08-20
EP1866960A1 (fr) 2007-12-19
US20060223937A1 (en) 2006-10-05
KR20070118139A (ko) 2007-12-13
JP2008536968A (ja) 2008-09-11
TW200703597A (en) 2007-01-16
KR101332702B1 (ko) 2013-11-25
ATE455371T1 (de) 2010-01-15
US20070117917A1 (en) 2007-05-24
CN101151726B (zh) 2010-06-23

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